The Ultimate Guide to Happy Hour Drinks at a Downtown Redlands Bar & Steakhouse

There’s a precise moment each day when the world shifts gears. Laptop screens dim, office lights flicker off, and suddenly the streets of downtown Redlands fill with people searching for something more than just the end of their workday. They’re seeking connection, relaxation, and that perfect drink that somehow makes everything feel right again. This is the golden hour—literally and figuratively—when happy hour transforms from a simple concept into an essential ritual.

The Downtown Redlands Advantage

Downtown Redlands possesses something increasingly rare in Southern California: genuine character. While other cities rush to demolish history in favor of generic development, Redlands has preserved its Victorian soul while welcoming contemporary energy. When you settle into a barstool at a downtown steakhouse during happy hour, you’re surrounded by architecture that has witnessed over a century of similar gatherings. The weight of that history adds depth to every sip.

The proximity to Interstate 10 means professionals from San Bernardino, Riverside, Loma Linda, and beyond can easily escape to Redlands for happy hour without fighting the soul-crushing traffic that plagues larger metropolitan areas. You arrive relaxed rather than frazzled, already halfway toward the mindset that makes happy hour truly effective.

What distinguishes a steakhouse bar from typical happy hour venues is the inherent commitment to quality that permeates everything. When an establishment stakes its reputation on perfectly cooking expensive cuts of beef, that same attention to detail flows into every cocktail, every wine pour, every beer selection. You’re not just getting discounts—you’re accessing excellence at accessible prices.

Whiskey: The Steakhouse Spirit

If steakhouses had an official beverage category, whiskey would win unanimously. The robust, complex flavors of aged spirits complement beef in ways that lighter alcohols simply cannot match. Understanding whiskey basics transforms you from someone who “drinks whiskey” into someone who appreciates it.

Bourbon represents American whiskey-making at its finest. By law, bourbon must contain at least 51% corn in its mash bill, aged in new charred oak barrels. This process creates those signature notes of vanilla, caramel, and butterscotch that make bourbon simultaneously comforting and complex. During happy hour, exploring different bourbon expressions—from the approachable smoothness of Maker’s Mark to the bold spice of Knob Creek—becomes financially feasible. Each distillery’s unique approach to fermentation, distillation, and aging creates distinct personalities worth discovering.

Rye whiskey brings entirely different characteristics to your glass. The higher percentage of rye grain creates spicier, more assertive flavors with notes of pepper, mint, and dried fruit. Where bourbon soothes, rye awakens. It’s the whiskey you choose when you want your drink to stand up and demand attention. In cocktails like Manhattans or Old Fashioneds, rye’s boldness prevents the drink from becoming too sweet, creating balance that bourbon sometimes struggles to achieve.

Irish whiskey offers approachability that makes it perfect for whiskey newcomers. Triple-distilled for smoothness, Irish whiskeys typically present lighter, more delicate flavor profiles with hints of honey and grain. They’re excellent served neat or with a single ice cube, allowing you to appreciate subtlety without overwhelming your palate.

Scotch whisky (note the spelling—Scots drop the “e”) encompasses an entire universe of flavors depending on the region of origin. Speyside Scotches tend toward elegant, fruity profiles. Highland expressions offer heather and honey notes. Islay malts bring powerful peat smoke that divides whisky drinkers into passionate lovers or adamant avoiders. Happy hour provides the perfect low-stakes opportunity to venture beyond your comfort zone—try that peated Scotch you’ve been curious about without committing to an expensive pour.

Cocktail Classics Reimagined

While certain cocktails have earned permanent positions in the steakhouse repertoire, the best bartenders understand that “classic” doesn’t mean “unchanging.” These are drinks with foundations solid enough to support creative interpretation.

The Sazerac predates even the Manhattan, originating in New Orleans during the 1830s. This drink showcases rye whiskey or cognac, with sugar, Peychaud’s bitters, and an absinthe rinse creating a cocktail that tastes like drinking perfumed history. The preparation ritual—chilling one glass while building the drink in another, then discarding the absinthe used to coat the serving glass—adds theater that elevates happy hour into performance art. Each sip delivers complexity: the spice of rye, the licorice hint of absinthe, the aromatic intensity of Peychaud’s bitters all dancing together.

Negronis have experienced a renaissance among cocktail enthusiasts, and deservedly so. Equal parts gin, Campari, and sweet vermouth create a drink that’s simultaneously bitter, sweet, and botanical. The Negroni doesn’t seduce you gently—it confronts you with bold flavors that some people need time to appreciate. Once you develop a taste for that distinctive bitterness, however, few cocktails satisfy quite the same way. It’s an aperitif that genuinely stimulates your appetite, making it ideal for starting an evening that will include a substantial meal.

The Boulevardier takes the Negroni’s template and substitutes bourbon or rye for gin, creating a richer, more American interpretation. The whiskey’s warmth softens Campari’s aggressive bitterness slightly while adding vanilla and oak notes that make the drink feel appropriate year-round. This cocktail particularly shines during cooler months when you want something robust and warming.

Paper Planes represent modern classics—cocktails invented recently but achieving widespread recognition through sheer deliciousness. Created in 2008, this drink combines bourbon, Aperol, Amaro Nonino, and fresh lemon juice in equal parts. The result tastes nothing like its individual components, instead creating a harmonious whole that’s simultaneously sweet, bitter, sour, and spirit-forward. It’s approachable enough for cocktail novices but interesting enough to captivate experienced drinkers.

Wine Wisdom for the Steakhouse Setting

Wine intimidates many people unnecessarily. The vocabulary, the rituals, the seemingly endless options—it all feels designed to make you feel inadequate. But happy hour provides the ideal environment for wine exploration because the financial stakes are lower and the atmosphere typically feels more relaxed than formal dinner service.

Understanding tannins transforms how you experience red wine. Tannins are compounds from grape skins, seeds, and stems that create that dry, puckering sensation in your mouth. When you drink a tannic wine like Cabernet Sauvignon alongside fatty beef, magic happens—the fat softens the tannins while the tannins cut through the richness. This is why Cabernet and steak have been partners for generations. During happy hour, try tasting your Cabernet first without food, then with a bite of something rich. The difference will be revelatory.

Tempranillo from Spain deserves far more attention than it typically receives. This grape produces wines with earthy, leathery characteristics balanced by red fruit and moderate tannins. It’s less aggressive than Cabernet but more structured than Merlot, occupying a sweet spot that pairs beautifully with grilled meats. Spanish Riojas, made primarily from Tempranillo, offer exceptional value and showcase how extended oak aging can add vanilla and spice notes without overwhelming the wine’s fundamental character.

Zinfandel is California’s adopted child—actually the Croatian grape Cribošnik, but so thoroughly associated with California that most people consider it native. Zinfandel produces jammy, fruit-forward wines with enough alcohol content to make them feel substantial. They’re not wines for contemplation—they’re wines for enjoyment, bringing berry flavors and often a slight sweetness that appeals to people who find drier reds too austere.

Syrah (called Shiraz in Australia) brings peppery, meaty characteristics that feel almost custom-designed for steakhouse environments. Northern Rhône Syrahs from France tend toward elegance and restraint, while Australian Shiraz often delivers bold, fruit-driven power. Both styles work wonderfully with beef, offering different but equally valid approaches to the pairing.

Craft Beer: Democracy in a Glass

Beer remains the most democratic of alcoholic beverages. It doesn’t demand special glassware, decanting, or detailed knowledge to enjoy. Yet the craft beer movement has elevated beer to a level of complexity that can rival wine when brewers choose to pursue it.

Pilsners and lagers provide refreshment that heavier beers cannot match. Despite craft beer’s tendency toward bigger, bolder styles, sometimes a crisp, clean lager tastes exactly right. Czech Pilsners like Pilsner Urquell offer slight hoppy bitterness balanced by bready malt character—these aren’t insipid lawn-mowing beers but legitimate expressions of brewer’s art. During happy hour, especially on warmer days, a perfectly poured pilsner can be more satisfying than any cocktail.

Hazy IPAs have transformed the craft beer landscape over the past decade. Unlike West Coast IPAs that emphasize crisp bitterness, New England-style hazies bring tropical fruit flavors and juicy character with softer bitterness. They look like orange juice and sometimes taste like liquid fruit salad. For people who thought they didn’t like IPAs, hazies often provide conversion experiences.

Belgian ales encompass a vast category unified more by yeast character than any other single factor. Belgian yeast strains produce fruity, spicy notes that make these beers taste complex even without additions. Dubbels, Tripels, and Saisons all originated in Belgium, showcasing how creative fermentation can produce radically different results from similar ingredients. These beers often feature higher alcohol content while remaining dangerously drinkable.

Sours represent beer’s wild side—literally, since many traditional sours result from wild yeast fermentation. Modern versions often achieve tartness through kettle souring, creating beers that pucker your mouth like lemonade. Berliner Weisse, Gose, and Flanders Red Ale all occupy the sour spectrum, offering alternatives to people who find standard beers too malt-forward or bitter.

Tequila and Mezcal: Beyond the Margarita

Agave spirits have suffered from unfortunate associations with late-night poor decisions and sugary blended drinks. But quality tequila and mezcal deserve serious consideration, especially in the steakhouse environment where their vegetal, earthy characteristics complement grilled flavors beautifully.

Tequila must be made from blue agave grown in specific Mexican regions. The production process—harvesting mature agave plants, cooking the piñas, fermenting, and distilling—creates spirits ranging from bright and citrusy (blanco) to rich and complex (añejo). Sipping quality blanco tequila neat reveals flavors that cheap mixto tequilas hide beneath additives. During happy hour, trying a proper tequila flight educates your palate while introducing you to Mexico’s national spirit as it’s meant to be experienced.

Mezcal encompasses all agave spirits made in designated Mexican regions, including tequila (though people typically use “mezcal” to refer to non-tequila agave spirits). Most mezcal comes from Oaxaca, where traditional production methods involve roasting agave in underground pits before fermentation. This creates that distinctive smoky character that defines mezcal for most drinkers. The spirit ranges from subtle and refined to aggressively smoky depending on production methods and agave varieties used.

Palomas deserve to replace margaritas as America’s default tequila cocktail. This simple combination of tequila, grapefruit soda (or fresh grapefruit juice with soda water), and lime tastes infinitely more refreshing than most margaritas while showcasing the tequila instead of burying it. During happy hour, a properly made Paloma with quality blanco tequila and fresh-squeezed grapefruit achieves perfection that frozen margaritas never approach.

The Psychology of Happy Hour Ordering

How you approach ordering during happy hour significantly impacts your experience. This isn’t just about maximizing value—it’s about strategic enjoyment.

Start lighter, progress darker generally serves you well across multiple drinks. Beginning with a crisp gin martini or light beer allows your palate to remain sensitive. As the evening progresses and you’ve had appetizers, transitioning to bourbon or red wine makes sense. Your taste buds adapt and can handle more robust flavors after initial sensitization.

Consider your dinner plans when ordering. If you’re staying for a full steakhouse meal after happy hour, avoid drinks that will overwhelm your palate before your entrée arrives. Conversely, if happy hour constitutes your entire evening, you can be more adventurous since you’re not preserving your palate for anything else.

Rotate categories across visits to prevent happy hour from becoming monotonous. If you defaulted to IPAs last week, explore cocktails this week. If you’ve been drinking whiskey consistently, branch into wine or tequila. This rotation keeps you engaged and prevents the routine from feeling stale.

Trust your bartender when you’re feeling indecisive. A simple “I normally like X, but I want to try something different” gives bartenders exactly the information they need to guide you toward satisfaction. Great bartenders take genuine pride in matching people with drinks they’ll love.

Food Pairings That Maximize Pleasure

Happy hour appetizers shouldn’t be afterthoughts—they’re essential components of the experience that dramatically affect how you perceive your drinks.

Oysters and gin martinis create one of gastronomy’s perfect marriages. The briny salinity of fresh oysters mirrors the botanical character of gin, while the martini’s cold, crisp nature refreshes your palate between each oyster. Add a squeeze of lemon to both, and you’ve created flavor harmony that transcends the sum of its parts.

Buffalo wings or spicy appetizers pair excellently with beer, particularly IPAs whose bitterness complements heat, or malty ambers whose sweetness provides relief. Wine generally struggles with genuinely spicy food, though off-dry Riesling can work beautifully if available.

Cheese and charcuterie boards offer versatility that allows pairing with almost any drink. Hard, aged cheeses match red wine’s tannins. Creamy cheeses work with white wine’s acidity. Salty cured meats complement beer’s malt character. This makes cheese boards ideal for groups where everyone’s drinking something different.

Crab cakes or shrimp cocktail showcase why steakhouses maintain seafood options. These lighter preparations pair wonderfully with Chardonnay, lighter beers, or even champagne. They prepare your palate for heavier courses without overwhelming it prematurely.

Building Your Happy Hour Community

Regular happy hour attendance creates social networks that enrich your life in unexpected ways. These relationships differ from workplace friendships or family connections—they’re chosen associations based purely on mutual enjoyment of a shared space and time.

Acknowledge familiar faces even before you know names. A simple nod or smile begins the process of transforming strangers into acquaintances. Eventually, conversations start naturally—comparing drink choices, discussing sports on the television, commenting on the weather. These small interactions accumulate into genuine camaraderie.

Bring different people from various parts of your life to happy hour. Introducing friends who’ve never met creates new connections while showing your happy hour spot to fresh eyes. Watching friends discover your favorite bartender’s cocktail expertise or taste that wine you’ve been raving about provides vicarious pleasure.

Respect the space and other patrons by maintaining appropriate volume and behavior. Happy hour should feel convivial without becoming obnoxious. The best regulars enhance the atmosphere for everyone through their positive presence rather than dominating attention.

Seasonal Drinking Strategies

Your drink preferences should evolve with California’s seasons, even if those seasons present subtler variations than other regions experience.

Summer demands refreshment above all else. This is when light lagers, gin and tonics, and crisp white wines reach their peak appeal. Frozen margaritas—often derided by cocktail purists—actually make perfect sense when temperatures spike. The steakhouse’s air conditioning provides relief, but your drink should too.

Fall brings comfort in the form of darker spirits and fuller wines. This is when bourbon truly shines, when Cabernet tastes most appropriate, when you start considering after-dinner drinks like port or dessert wines. The changing leaves (yes, even in Southern California) and earlier sunsets create psychological shifts that influence what tastes good.

Winter encourages contemplation through whiskey flights, bold reds, and occasionally even hot cocktails. While Redlands rarely experiences true cold, the shorter days and occasional rain create moods that match darker, richer drinks perfectly.

Spring renewal manifests in lighter reds, aromatic whites, and cocktails featuring fresh herbs. This is when muddled mint, basil, or cucumber start appearing in drinks, when rosé transitions from guilty pleasure to obviously correct choice.

The Economics of Smart Happy Hour Participation

Understanding happy hour’s financial dynamics helps you maximize value without appearing cheap or calculating.

Premium pours at happy hour prices represent genuine value. When a steakhouse offers top-shelf spirits during happy hour, they’re essentially giving you access to quality that would otherwise feel prohibitively expensive. This isn’t the time to order rail vodka—explore those premium bottles you’re curious about.

Wine by the glass during happy hour often costs less than retail wine shop prices for the same bottle. If you’re comparing a $10 happy hour glass from a $40 bottle, you’re essentially paying below retail while someone else handles storage, serving temperature, and glassware.

Appetizer combinations strategically chosen can constitute legitimate meals at dinner entrée prices. Pairing drinks with several small plates during extended happy hour creates satisfying evenings that cost considerably less than full dinner service.

Skip the upsells you don’t genuinely want. Happy hour’s appeal lies in value, but that value disappears when you’re pressured into premium additions you wouldn’t normally choose. A perfectly made standard margarita beats an overpriced top-shelf version you didn’t actually desire.

The Tartan of Redlands Commitment

At Tartan of Redlands, we’ve designed our happy hour to honor both tradition and innovation. Our downtown location immerses you in Redlands’ historic charm while providing thoroughly modern comfort and quality.

Our bar program reflects serious thought and care. We’ve selected spirits, wines, and beers that represent quality across price points, ensuring happy hour offerings maintain the standards we apply throughout our operations. Our bartenders bring expertise earned through years of practice, not just memorized recipes. They understand that making drinks well requires technical skill, creativity, and genuine interest in your satisfaction.

We’ve created an environment where professionals unwind without pretension, where dates unfold naturally, where friends reconnect over drinks that taste like someone cares. Our happy hour isn’t about moving inventory or meeting quotas—it’s about providing value to our community while introducing people to the quality that defines everything we do.

The appetizers we’ve designed specifically complement our drink offerings. From classic shrimp cocktail to innovative seasonal creations featuring locally sourced ingredients, every small plate reflects the same attention to detail we apply to our renowned steaks. This ensures your happy hour experience feels cohesive and intentional rather than assembled from random components.

Visit us and discover why downtown Redlands residents consistently choose Tartan of Redlands when they want happy hour to mean something more than discounted drinks. Make your reservation, gather your colleagues or friends, and let us demonstrate what happy hour should truly deliver: quality drinks, welcoming atmosphere, and experiences worth repeating.

About the Restaurant

Tartan of Redlands is a classic local steakhouse celebrated for its Saturday Prime Rib, diverse steak selections, the iconic Redlands Tartan Burger, and a fully stocked bar. This iconic spot first welcomed guests on April 15, 1964, thanks to the vision of three brothers—Velmer, Al, and Art Ctoteau.

Larry Westin took over managing the restaurant and later became a partner alongside the Ctoteau brothers. Mr. and Mrs. Westin remained at the helm until his passing in 2003, after which the restaurant was entrusted to Larry Westin Jr. He upheld the family tradition until 2015, when Tartan of Redlands was sold to its current owners, Jeff and Lisa Salamon.

Jeff hails from Boston, Massachusetts, and is a proud veteran of the United States Marine Corps. Even with the changes in ownership, you will find that the old-school atmosphere has remained and the reputation of being the Cheers of Redlands where everybody knows your name remains strong.